


The Dildo Dare

by EnInkahootz



Category: Supernatural
Genre: Alcohol, Anal Fingering, Anal Sex, Barebacking, Bottom Dean Winchester, Bottom Dean Winchester/Top Sam Winchester, Brother/Brother Incest, Brothers, Come, Dildos, Drunk Sex, First Time, Incest, M/M, Porn, Romance, Sex Toys Under Clothing, Sibling Incest, Smut, Supernatural Kink Bingo 2021, Top Sam Winchester, Truth or Dare
Language: English
Status: Completed
Published: 2021-01-28
Updated: 2021-01-28
Packaged: 2021-03-13 21:13:50
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,924
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29035233
Author URL: https://archiveofourown.org/users/EnInkahootz/pseuds/EnInkahootz
Summary: Sam and Dean get drunk and play Truth or Dare.  Sam dares Dean to spend the rest of the night with a dildo in his ass.
Relationships: Dean Winchester/Sam Winchester
Comments: 3
Kudos: 305
Collections: SPN Kink Bingo 2021





	The Dildo Dare

**Author's Note:**

> Written for SPN Kink Bingo 2021 square: Dildo

“You know my answer, Sammy,” Dean replied with a grin, his body swaying slightly, “dare all the way.” He downed the remainder of his drink before adding, “go on, give me your best shot.” Sometimes when the brothers were drunk enough they played Truth or Dare, like they had when they were growing up. Dean enjoyed the flavor of the activity, the delightful mix of innocent play and troublemaking.

“Hmm,” Sam said, his face one of drunken consideration until it broke suddenly into a mischievous grin, “I dare you to put your dildo in your ass and keep it there for the rest of the night.”

“I don’t have a dildo,” Dean said far too quickly.

“Dude, I’ve seen it. Don’t lie. Do you accept the dare?”

Dean felt himself flush, but after a few beats he nodded.

“Excellent,” Sam said, “go get it, bring it here.”

Dean gawked at him.

“I mean, you’re not gonna watch me put it in or anything.”

“Sure am,” Sam replied, “how else do I know you’re really doing it?”

Dean struggled to read Sam’s face, but he was too drunk to tell if there was lust there or not. He hoped there was, but he tried to pretend, even to his drunken self, that he hoped there wasn’t. He tried to pretend that he hoped Sam was just trying to find a good dare and meant nothing by it. He tried to pretend that he didn’t want Sam more than anything in all of existence.

“Uh,” Dean replied, “I guess… okay, be right back.”

Dean went to his room in the Bunker and retrieved his dildo from the bottom drawer of his dresser where he kept it beneath a pile of boxers and socks. He also grabbed a bottle of lube from the drawer in his nightstand, then returned to the library, trying to act casual; this was just another dare, nothing weird or sexual about it.

“Want me to put it in for you?” Sam asked as though it was a completely normal suggestion.

“Um,” was all Dean could think to say. He very much wanted Sam to put it in for him; the strength of his desire for it stunned him, rendered him unable to move or speak. Too many silent minutes passed.

“I want to do it for you, Dean,” Sam finally said, “is that okay?” and before Dean could stop himself he was nodding in eager agreement. Sam made a low, pleased hum in response and undid Dean’s pants, then pushed them to his ankles along with the boxer shorts beneath. Dean was too shocked and drunk to know what to do, and so he simply stood there stupidly and let his bottom half be undressed, realizing too late that his cock had hardened. Sam’s eyes fell to Dean’s erection when it was revealed.

“Um,” Dean said again.

“You really like the dare, huh?” Sam asked with a slightly wicked smirk as he took the dildo and lube from Dean’s hands.

Dean made a forced laugh, not sure what else to do. He thought about pulling his pants up and shoving his erection behind the fabric of his fly and calling it a night; they were obviously too drunk. He tried to do it, but he couldn’t bring himself to put an end to whatever was happening. As wrong as he knew it was to be doing anything sexual with his brother, Dean could no longer resist his longing for Sam, a longing that had lived in him for their entire adult lives, a longing that Dean spent constant energy straining to ignore. Now that Sam had encouraged Dean’s lust, resistance seemed simply and factually impossible. Dean cleared his throat and hurried to compose himself as best he could.

“So, should I bend over the table?” he asked, hearing that his voice was shaky even though he had meant it to be smooth.

“Yeah, Dean,” Sam replied, and this time Dean could see the lust radiating from his face, could hear it dripping from his voice, “bend over the table.”

With a rapidly beating heart Dean did so, and he felt Sam come up behind him. He looked back at Sam over his shoulder and Sam gave him a tender, reassuring smile. Dean felt a wave of calm at the sight. He leaned his head on his folded arms and took a few deep breaths, tingling with anticipation. He heard the sound of Sam opening the bottle of lube followed by the wet noise of him pouring some into his hand.

“Ready for me to touch you?”

“Yeah, Sammy, touch me,” Dean groaned.

After a brief pause Dean felt Sam’s slippery fingers nuzzle between the cheeks of his ass. Dean gasped at the moment of contact and Sam responded with a short, hungry moan. Sam’s fingers found Dean’s hole and a sharp thrill ran through Dean’s being. Gently, Sam spread lube over the sensitive space. 

“Doing okay?” Sam asked.

“Fuck yes,” Dean murmured.

“Good,” Sam said as he began to run the tip of his forefinger around the puckered rim of Dean’s hole. Dean started a long groan as he strained not to shove his ass back against Sam’s touch and wiggle his hips until Sam’s finger slipped inside.

“You want my fingers inside you?” Sam asked as though he could feel Dean’s desperation.

“Yeah, Sammy, please.”

“Oh fuck yes,” Sam grunted as he slid two fingers gradually into Dean’s channel. Sam held his hand still for a moment and Dean was glad for the chance to relish the initial penetration. In time, though, Sam’s fingers began to move. They glided slowly outward and then fully inside once again. They twisted to and fro and stretched Dean’s entrance with a scissoring motion. Sam added a third finger and Dean muttered his brother’s name without meaning to. Sam spread his fingers within Dean’s tightness, then curled them and rubbed Dean’s most sensitive spot. Dean cried out, lost in the pleasure.

Dean didn’t know how long passed with Sam’s fingers inside him, filling him and stretching him and touching every spot within him, but he felt like he could have welcomed the decadent sensations forever. When Sam finally withdrew his fingers, Dean made a needy sound of loss and Sam chuckled fondly.

“Ready for the dildo?” Sam asked. Dean had almost forgotten about the dare.

“Yeah, yes, put it in me,” he breathed.

“Dean,” Sam spoke with yearning. Dean heard him pick up the dildo and slick it with lube. He felt Sam slip the dildo between his cheeks and then he felt the dildo’s head press to his entrance.

“Ready?” Sam asked again.

“Yes,” Dean replied desperately, “do it, do it, Sammy.”

At that Sam began to push the dildo into him. The penetration was not rough, but neither was it slow, and soon Dean was filled with the firm toy. His cock pulsed against the table beneath him.

“How does it feel?” Sam asked.

“So fucking good.”

“Do you fuck yourself with this when you jerk off?” Sam asked, though it was clear from his tone that he knew the answer.

“Yeah,” Dean replied, feeling his body flush.

“I want to fuck you with it.”

“Um,” Dean said, overwhelmed, “yeah, yes, please.”

Sam pulled the dildo nearly all the way out at an excruciatingly slow pace, then pushed it back in just as slowly. He repeated the motions over and again, and each time the dildo was fully inside Sam paused to spend a moment holding it in as deeply as it could possibly reach, keeping Dean blissfully filled for a stretched-out instant before he drew back the toy once again. Dean moaned and fought his instinct to hump the table.

“Does it feel better than when you fuck yourself?”

“So much better,” Dean panted.

“Dean,” Sam spoke in a low, serious tone, “I’m hard for you.”

“Sammy…”

“My cock is so hard for you, Dean, it wants to be where the dildo is. It wants it so badly, oh fuck, Dean, do you want my cock?”

“Sammy, yes, yes, fuck me.”

He felt Sam remove the dildo and then he heard Sam’s zipper and the slick sound of him lubing his cock. Dean’s cock throbbed beneath him and his head spun with desire and disbelief that his brother was really about to fuck him, that his fantasies were finally going to come true. Sam guided his hardness to Dean’s entrance and paused, the head of his cock pressed lightly to Dean’s hole.

“Inside, inside, please,” Dean begged.

“Oh Dean, oh fuck,” Sam groaned urgently, then pushed himself all the way in.

“Oh my god, Sammy,” Dean spoke with awe, feeling encompassed by a sense of sheer joy, blinding joy, joy that made him forget everything else.

“Good?” Sam panted.

“So good, you feel so good inside me, oh please fuck me, fuck me hard, Sammy, I need you so bad.”

“Dean,” Sam moaned, and he began to pound into him, gripping Dean’s hips and working his cock in and out of Dean’s ass at rapid speed. His sounds and movements were wild, possessive, and Dean felt perfectly claimed.

“Fuck me, fuck me,” he whispered, “Sammy, Sammy.”

“You feel so fucking good, Dean,” Sam told him, and Dean felt warm and pleased at the compliment, “oh, fuck, I’ve wanted this for so long.”

“What?” Dean asked with shock.

“Haven’t you?”

“Yes,” Dean admitted, the small word overflowing with feeling.

They fucked wordlessly for a time after that, but Dean felt like he could feel Sam’s every unspoken emotion, could sense the complex meaning of his every movement. He felt so close to Sam that he thought they might melt into each other and become one single unit, even more so than they already were. He finally allowed himself to hump the table beneath him and their sounds of need overlapped as Dean’s orgasm drew near. Sam’s speed increased, his hips snapping forcefully, his rapid motion causing Dean’s cock to rub briskly against the surface of the table. Sam’s cock was massive, and it touched every sensitive spot within Dean’s channel as it filled him again and again. Dean listened to his brother’s grunts and moans and groans, to his eager breath growing heavier and heavier.

“I’m coming, coming for you, Dean,” Sam suddenly yelled, and Dean hurried to let go, managing to release in the same moment as his brother, Sam shooting deep into Dean’s body as Dean spilled his seed onto the table. He cried out Sam’s name as he climaxed, his whole body throbbing with ecstasy, glowing with satiation and an already building longing for more of Sam’s nearness, for more of his hard cock and his fierce desire.

After they had both come down from the peaks of their pleasure, Sam pulled his cock out, then quickly replaced it with the dildo, trapping his cum inside Dean’s body. Still panting, he guided Dean upright, then pulled up Dean’s boxers and pants and closed up his fly, the dildo and Sam’s seed now concealed beneath his clothing. 

“Okay,” Sam breathed, “for my turn I’ll take a dare too.”

“What?” Dean asked hazily.

“Aren’t we still playing?”

“Huh?”

“Truth or Dare, remember?”

“Oh, right,” Dean said with a gentle laugh, vaguely recalling life before their sex, “yeah, I’ll play longer. I’ll pour us some fresh drinks.”

They stayed up for a few more hours, drinking and playing the game, all the while Dean’s dildo and Sam’s cum hidden snugly within Dean’s ass.


End file.
